I have tested this many times and the same thing occurs each time. On my MacBook Pro, when I plug in my headphones while playing wizard101 no sound comes from the game. But the sound works on every other application. In fact, even after removing the headphones, the sound cannot be resumed in the application until it has been restarted. I don't know if this is a problem with Wizard101, or the WineBottler it uses, but I thought it should be reported.